# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_wzt-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2269106'
loop_
_audit_author_name
_audit_author_address
'zhiting wang'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2023-06-12 deposited with the CCDC.	2023-12-08 downloaded from the CCDC.
;
_audit_creation_date             2022-01-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H27 N O2'
_chemical_formula_sum            'C22 H27 N O2'
_chemical_formula_weight         337.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20O2N1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5717(3)
_cell_length_b                   9.8552(4)
_cell_length_c                   10.5251(3)
_cell_angle_alpha                90.752(3)
_cell_angle_beta                 90.752(3)
_cell_angle_gamma                102.176(3)
_cell_volume                     970.31(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4356
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.0600
_cell_measurement_theta_min      5.8500
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.904
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7024
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.936
_diffrn_reflns_theta_min         4.201
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -23.00   1.00    1.00    --  -41.76 -38.00   0.00   92
  2  ω     29.00  57.00   1.00    1.00    --   41.76-125.00 -30.00   28
  3  ω     20.00  81.00   1.00    1.00    --   41.76 -99.00  30.00   61
  4  ω     35.00  71.00   1.00    1.00    --   41.76-125.00 -60.00   36
  5  ω     82.00 128.00   1.00    3.00    --  106.05  30.00 -90.00   46
  6  ω    131.00 170.00   1.00    3.00    --  106.05  30.00 -90.00   39
  7  ω    109.00 171.00   1.00    3.00    --  106.05  77.00 -60.00   62
  8  ω    153.00 178.00   1.00    3.00    --  106.05  61.00 -30.00   25
  9  ω     90.00 116.00   1.00    3.00    --  106.05  61.00 -30.00   26
 10  ω     34.00 132.00   1.00    3.00    --  106.05 -45.00-180.00   98
 11  ω     39.00 129.00   1.00    3.00    --  106.05 -30.00 -30.00   90
 12  ω    -35.00 -10.00   1.00    1.00    --  -42.01 125.00 150.00   25
 13  ω   -116.00 -29.00   1.00    1.00    --  -42.01 -38.00 -90.00   87
 14  ω    -11.00  56.00   1.00    1.00    --   42.01 -77.00 120.00   67
 15  ω     55.00 112.00   1.00    3.00    --  106.05-125.00 120.00   57
 16  ω     61.00 138.00   1.00    3.00    --  106.05 -77.00 -90.00   77
 17  ω     44.00 106.00   1.00    3.00    --  106.05 -94.00-150.00   62
 18  ω     87.00 112.00   1.00    3.00    --  106.05-125.00   0.00   25
 19  ω     88.00 139.00   1.00    3.00    --  106.05  61.00   0.00   51
 20  ω    114.00 155.00   1.00    3.00    --  106.05 125.00-120.00   41
 21  ω    107.00 133.00   1.00    3.00    --  106.05  77.00 150.00   26
 22  ω     54.00  96.00   1.00    3.00    --  106.05 -94.00 150.00   42
 23  ω     85.00 110.00   1.00    3.00    --  106.05-125.00  60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0219314000
_diffrn_orient_matrix_UB_12      -0.1479210000
_diffrn_orient_matrix_UB_13      0.0245103000
_diffrn_orient_matrix_UB_21      0.0990985000
_diffrn_orient_matrix_UB_22      0.0550760000
_diffrn_orient_matrix_UB_23      0.1141394000
_diffrn_orient_matrix_UB_31      -0.1296775000
_diffrn_orient_matrix_UB_32      -0.0258080000
_diffrn_orient_matrix_UB_33      0.0883458000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3255
_reflns_number_total             3741
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0184(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3741
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0836P)²+0.1583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1647
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C1(H1), C6(H6)
1.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C2(H2A,H2B), C9(H9A,H9B), C5(H5A,H5B), C3(H3A,H3B), C4(H4A,H4B)
1.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C20(H20), C11(H11), C15(H15), C22(H22), C21(H21), C12(H12),
 C19(H19), C14(H14), C13(H13)
1.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.33886(12) 0.53741(11) 0.77897(11) 0.0469(3) Uani 1 1 d . . . . .
O2 O 0.30322(14) 0.56279(15) 0.45181(12) 0.0772(4) Uani 1 1 d . . . . .
O1 O 0.20667(18) 0.71554(18) 0.55842(15) 0.0967(5) Uani 1 1 d . . . . .
C1 C 0.42432(15) 0.67626(14) 0.75351(13) 0.0482(3) Uani 1 1 d . . . . .
H1 H 0.3666 0.7424 0.7802 0.058 Uiso 1 1 calc R U . . .
C17 C 0.18943(16) 0.62392(15) 0.94051(14) 0.0538(4) Uani 1 1 d . . . . .
C16 C 0.28312(18) 0.52435(16) 0.90756(14) 0.0563(4) Uani 1 1 d . . . . .
H16A H 0.3630 0.5387 0.9674 0.068 Uiso 1 1 calc R U . . .
H16B H 0.2288 0.4304 0.9179 0.068 Uiso 1 1 calc R U . . .
C10 C 0.30501(18) 0.28600(16) 0.73168(15) 0.0588(4) Uani 1 1 d . . . . .
C6 C 0.44750(17) 0.69647(16) 0.61081(15) 0.0559(4) Uani 1 1 d . . . . .
H6 H 0.5079 0.6342 0.5807 0.067 Uiso 1 1 calc R U . . .
C2 C 0.56693(18) 0.71751(18) 0.82616(18) 0.0646(4) Uani 1 1 d . . . . .
H2A H 0.5504 0.7069 0.9166 0.078 Uiso 1 1 calc R U . . .
H2B H 0.6291 0.6563 0.8009 0.078 Uiso 1 1 calc R U . . .
C9 C 0.41002(17) 0.42267(15) 0.75185(16) 0.0563(4) Uani 1 1 d . . . . .
H9A H 0.4741 0.4142 0.8221 0.068 Uiso 1 1 calc R U . . .
H9B H 0.4671 0.4435 0.6763 0.068 Uiso 1 1 calc R U . . .
C7 C 0.30571(19) 0.66194(19) 0.54014(15) 0.0634(4) Uani 1 1 d . . . . .
C18 C 0.07645(18) 0.6367(2) 0.86298(19) 0.0705(5) Uani 1 1 d . . . . .
H18 H 0.0604 0.5862 0.7870 0.085 Uiso 1 1 calc R U . . .
C20 C 0.0088(3) 0.7984(2) 1.0088(3) 0.0913(7) Uani 1 1 d . . . . .
H20 H -0.0527 0.8556 1.0321 0.110 Uiso 1 1 calc R U . . .
C11 C 0.3293(2) 0.16576(18) 0.7847(2) 0.0772(5) Uani 1 1 d . . . . .
H11 H 0.4089 0.1688 0.8370 0.093 Uiso 1 1 calc R U . . .
C15 C 0.1826(2) 0.2777(2) 0.65629(18) 0.0756(5) Uani 1 1 d . . . . .
H15 H 0.1628 0.3580 0.6215 0.091 Uiso 1 1 calc R U . . .
C5 C 0.5220(2) 0.8469(2) 0.5842(2) 0.0789(6) Uani 1 1 d . . . . .
H5A H 0.5412 0.8565 0.4941 0.095 Uiso 1 1 calc R U . . .
H5B H 0.4590 0.9084 0.6067 0.095 Uiso 1 1 calc R U . . .
C3 C 0.6397(2) 0.8669(2) 0.8000(2) 0.0824(6) Uani 1 1 d . . . . .
H3A H 0.5813 0.9288 0.8321 0.099 Uiso 1 1 calc R U . . .
H3B H 0.7313 0.8891 0.8444 0.099 Uiso 1 1 calc R U . . .
C22 C 0.2116(2) 0.7022(2) 1.05196(19) 0.0757(5) Uani 1 1 d . . . . .
H22 H 0.2886 0.6966 1.1050 0.091 Uiso 1 1 calc R U . . .
C21 C 0.1213(3) 0.7885(2) 1.0857(2) 0.0955(8) Uani 1 1 d . . . . .
H21 H 0.1375 0.8400 1.1611 0.115 Uiso 1 1 calc R U . . .
C12 C 0.2341(3) 0.0389(2) 0.7599(3) 0.1000(8) Uani 1 1 d . . . . .
H12 H 0.2511 -0.0419 0.7959 0.120 Uiso 1 1 calc R U . . .
C4 C 0.6620(2) 0.8893(2) 0.6597(3) 0.0952(7) Uani 1 1 d . . . . .
H4A H 0.7292 0.8353 0.6298 0.114 Uiso 1 1 calc R U . . .
H4B H 0.7030 0.9864 0.6454 0.114 Uiso 1 1 calc R U . . .
C19 C -0.0138(2) 0.7235(2) 0.8963(3) 0.0877(6) Uani 1 1 d . . . . .
H19 H -0.0897 0.7313 0.8428 0.105 Uiso 1 1 calc R U . . .
C14 C 0.0900(3) 0.1513(3) 0.6326(2) 0.0951(7) Uani 1 1 d . . . . .
H14 H 0.0090 0.1475 0.5817 0.114 Uiso 1 1 calc R U . . .
C13 C 0.1164(3) 0.0331(2) 0.6830(3) 0.1014(8) Uani 1 1 d . . . . .
H13 H 0.0547 -0.0516 0.6655 0.122 Uiso 1 1 calc R U . . .
C8 C 0.1725(3) 0.5260(3) 0.3760(2) 0.1089(9) Uani 1 1 d . . . . .
H8A H 0.1888 0.4732 0.3025 0.163 Uiso 1 1 calc R U . . .
H8B H 0.1437 0.6090 0.3496 0.163 Uiso 1 1 calc R U . . .
H8C H 0.0985 0.4715 0.4258 0.163 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.4686(17) . ?
N1 C16 1.4586(19) . ?
N1 C9 1.4648(18) . ?
O2 C7 1.336(2) . ?
O2 C8 1.452(3) . ?
O1 C7 1.195(2) . ?
C1 H1 0.9800 . ?
C1 C6 1.531(2) . ?
C1 C2 1.531(2) . ?
C17 C16 1.503(2) . ?
C17 C18 1.374(2) . ?
C17 C22 1.385(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C10 C9 1.512(2) . ?
C10 C11 1.378(2) . ?
C10 C15 1.394(3) . ?
C6 H6 0.9800 . ?
C6 C7 1.511(2) . ?
C6 C5 1.535(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.520(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C18 H18 0.9300 . ?
C18 C19 1.384(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.359(4) . ?
C20 C19 1.377(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.402(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.386(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.526(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.508(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.381(3) . ?
C21 H21 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.369(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C19 H19 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.356(4) . ?
C13 H13 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N1 C1 113.09(11) . . ?
C16 N1 C9 109.34(11) . . ?
C9 N1 C1 114.98(11) . . ?
C7 O2 C8 115.52(16) . . ?
N1 C1 H1 106.3 . . ?
N1 C1 C6 110.93(12) . . ?
N1 C1 C2 116.07(12) . . ?
C6 C1 H1 106.3 . . ?
C6 C1 C2 110.23(12) . . ?
C2 C1 H1 106.3 . . ?
C18 C17 C16 120.99(15) . . ?
C18 C17 C22 118.04(16) . . ?
C22 C17 C16 120.94(16) . . ?
N1 C16 C17 114.50(12) . . ?
N1 C16 H16A 108.6 . . ?
N1 C16 H16B 108.6 . . ?
C17 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C11 C10 C9 121.02(17) . . ?
C11 C10 C15 118.18(17) . . ?
C15 C10 C9 120.78(15) . . ?
C1 C6 H6 109.0 . . ?
C1 C6 C5 110.43(14) . . ?
C7 C6 C1 110.02(12) . . ?
C7 C6 H6 109.0 . . ?
C7 C6 C5 109.46(14) . . ?
C5 C6 H6 109.0 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 C1 111.15(15) . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
N1 C9 C10 112.37(12) . . ?
N1 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
O2 C7 C6 111.64(14) . . ?
O1 C7 O2 122.92(17) . . ?
O1 C7 C6 125.44(17) . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 120.95(19) . . ?
C19 C18 H18 119.5 . . ?
C21 C20 H20 120.1 . . ?
C21 C20 C19 119.83(19) . . ?
C19 C20 H20 120.1 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.1(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C15 H15 119.6 . . ?
C14 C15 C10 120.8(2) . . ?
C14 C15 H15 119.6 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C4 C5 C6 111.34(16) . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.08(17) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C17 C22 H22 119.5 . . ?
C21 C22 C17 121.1(2) . . ?
C21 C22 H22 119.5 . . ?
C20 C21 C22 120.1(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 C5 111.59(16) . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0(2) . . ?
C20 C19 H19 120.0 . . ?
C15 C14 H14 119.7 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14 119.7 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C6 C7 52.63(16) . . . . ?
N1 C1 C6 C5 173.56(13) . . . . ?
N1 C1 C2 C3 -175.45(14) . . . . ?
C1 N1 C16 C17 58.86(17) . . . . ?
C1 N1 C9 C10 -158.49(13) . . . . ?
C1 C6 C7 O2 -122.91(15) . . . . ?
C1 C6 C7 O1 57.5(2) . . . . ?
C1 C6 C5 C4 55.5(2) . . . . ?
C1 C2 C3 C4 -56.8(2) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C17 C22 C21 C20 -0.3(3) . . . . ?
C16 N1 C1 C6 -165.39(12) . . . . ?
C16 N1 C1 C2 67.79(16) . . . . ?
C16 N1 C9 C10 73.04(16) . . . . ?
C16 C17 C18 C19 176.95(17) . . . . ?
C16 C17 C22 C21 -176.67(17) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C10 C15 C14 C13 0.4(3) . . . . ?
C6 C1 C2 C3 57.39(18) . . . . ?
C6 C5 C4 C3 -55.1(2) . . . . ?
C2 C1 C6 C7 -177.40(13) . . . . ?
C2 C1 C6 C5 -56.46(17) . . . . ?
C2 C3 C4 C5 55.4(2) . . . . ?
C9 N1 C1 C6 68.04(15) . . . . ?
C9 N1 C1 C2 -58.78(17) . . . . ?
C9 N1 C16 C17 -171.63(12) . . . . ?
C9 C10 C11 C12 -176.93(17) . . . . ?
C9 C10 C15 C14 176.75(17) . . . . ?
C7 C6 C5 C4 176.76(16) . . . . ?
C18 C17 C16 N1 51.3(2) . . . . ?
C18 C17 C22 C21 1.3(3) . . . . ?
C11 C10 C9 N1 -136.91(16) . . . . ?
C11 C10 C15 C14 -1.7(3) . . . . ?
C11 C12 C13 C14 -1.3(4) . . . . ?
C15 C10 C9 N1 44.7(2) . . . . ?
C15 C10 C11 C12 1.5(3) . . . . ?
C15 C14 C13 C12 1.2(4) . . . . ?
C5 C6 C7 O2 115.58(16) . . . . ?
C5 C6 C7 O1 -64.0(2) . . . . ?
C22 C17 C16 N1 -130.79(16) . . . . ?
C22 C17 C18 C19 -1.0(3) . . . . ?
C21 C20 C19 C18 1.1(3) . . . . ?
C19 C20 C21 C22 -0.9(3) . . . . ?
C8 O2 C7 O1 1.5(3) . . . . ?
C8 O2 C7 C6 -178.02(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.182
_oxdiff_exptl_absorpt_empirical_full_min 0.778
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_wzt-1202_auto
_database_code_depnum_ccdc_archive 'CCDC 2311722'
loop_
_audit_author_name
_audit_author_address
wzt
;University of Science and Technology of China
China
;
_audit_update_record             
;
2023-12-02 deposited with the CCDC.	2023-12-08 downloaded from the CCDC.
;
_audit_creation_date             2023-12-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H38 N2 O3'
_chemical_formula_sum            'C33 H38 N2 O3'
_chemical_formula_weight         510.65
_chemical_absolute_configuration AD
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1O1N1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.80990(10)
_cell_length_b                   8.93610(10)
_cell_length_c                   18.6704(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.5870(10)
_cell_angle_gamma                90
_cell_volume                     1449.32(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15075
_cell_measurement_temperature    300
_cell_measurement_theta_max      72.4850
_cell_measurement_theta_min      4.7840
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.892
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27277
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.908
_diffrn_reflns_theta_min         4.804
_diffrn_ambient_temperature      300
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -13.00   1.00    1.00    --  -41.51 -57.00-180.00  101
  2  ω   -116.00 -17.00   1.00    1.00    --  -41.51 -38.00  60.00   99
  3  ω    -66.00  33.00   1.00    1.00    --  -41.51  38.00-120.00   99
  4  ω     61.00 130.00   1.00    1.00    --   41.51 178.00 120.00   69
  5  ω     17.00 116.00   1.00    1.00    --   41.51  38.00   0.00   99
  6  ω      6.00  81.00   1.00    1.00    --   41.51 -99.00 -60.00   75
  7  ω     77.00 178.00   1.00    1.00    --  105.74  30.00 120.00  101
  8  ω     23.00 107.00   1.00    1.00    --  105.74 -94.00-150.00   84
  9  ω     33.00 132.00   1.00    1.00    --  105.74 -45.00-180.00   99
 10  ω     53.00 178.00   1.00    1.00    --  105.74  15.00-150.00  125
 11  ω    103.00 178.00   1.00    1.00    --  105.74  77.00-150.00   75
 12  ω     35.00 113.00   1.00    1.00    --  105.74-125.00  30.00   78
 13  ω    103.00 178.00   1.00    1.00    --  105.74  77.00 -90.00   75
 14  ω    103.00 178.00   1.00    1.00    --  105.74  77.00 -90.00   75
 15  ω     35.00 113.00   1.00    1.00    --  105.74-125.00-150.00   78
 16  ω     77.00 178.00   1.00    1.00    --  105.74  30.00  60.00  101
 17  ω     77.00 178.00   1.00    1.00    --  105.74  61.00   0.00  101
 18  ω     35.00 113.00   1.00    1.00    --  105.74-125.00-150.00   78
 19  ω     77.00 178.00   1.00    1.00    --  105.74  30.00   0.00  101
 20  ω     97.00 177.00   1.00    1.00    --  105.74 125.00 -90.00   80
 21  ω    103.00 178.00   1.00    1.00    --  105.74  77.00 120.00   75
 22  ω     97.00 177.00   1.00    1.00    --  105.74 125.00 -90.00   80
 23  ω   -114.00 -11.00   1.00    1.00    --  -41.51 -66.00-113.00  103
 24  ω   -114.00 -13.00   1.00    1.00    --  -41.51 -57.00   0.00  101
 25  ω   -114.00 -13.00   1.00    1.00    --  -41.51 -57.00 -90.00  101
 26  ω   -114.00 -13.00   1.00    1.00    --  -41.51 -57.00 150.00  101
 27  ω   -114.00 -13.00   1.00    1.00    --  -41.51 -57.00  90.00  101
 28  ω    -21.00  74.00   1.00    1.00    --   41.51 -77.00  60.00   95
 29  ω     77.00 178.00   1.00    1.00    --  105.74  61.00 -90.00  101
 30  ω     77.00 131.00   1.00    1.00    --  105.74  61.00  60.00   54
 31  ω     77.00 178.00   1.00    1.00    --  105.74  61.00 -60.00  101
 32  ω     77.00 178.00   1.00    1.00    --  105.74  61.00-180.00  101
 33  ω     77.00 178.00   1.00    1.00    --  105.74  61.00-120.00  101
 34  ω     23.00 107.00   1.00    1.00    --  105.74 -94.00  60.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0252735000
_diffrn_orient_matrix_UB_12      -0.1411505000
_diffrn_orient_matrix_UB_13      -0.0439058000
_diffrn_orient_matrix_UB_21      0.1611133000
_diffrn_orient_matrix_UB_22      -0.0197614000
_diffrn_orient_matrix_UB_23      0.0458093000
_diffrn_orient_matrix_UB_31      -0.0696905000
_diffrn_orient_matrix_UB_32      -0.0969874000
_diffrn_orient_matrix_UB_33      0.0545501000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                5352
_reflns_number_total             5690
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 2322 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_coef       0.0355(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5690
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0710P)²+0.0897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1169
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02 within 2A
3.a Ternary CH refined with riding coordinates:
 C8(H8), C14(H14), C19(H19)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B),
 C20(H20A,H20B), C27(H27A,H27B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C22(H22), C23(H23), C24(H24),
 C25(H25), C26(H26), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6036(2) 0.6797(2) 0.10960(9) 0.0730(5) Uani 1 1 d . . . . .
C1 C 0.9942(5) 0.5745(9) 0.4338(3) 0.181(3) Uani 1 1 d . U . . .
H1 H 0.911095 0.509000 0.428758 0.217 Uiso 1 1 calc R U . . .
N1 N 0.6880(2) 0.5823(2) 0.22562(10) 0.0584(4) Uani 1 1 d . . . . .
O2 O 0.6777(2) 0.8264(2) 0.20518(9) 0.0736(5) Uani 1 1 d . . . . .
C2 C 1.0801(6) 0.6036(11) 0.5025(3) 0.199(3) Uani 1 1 d . U . . .
H2 H 1.049246 0.560118 0.543045 0.239 Uiso 1 1 calc R U . . .
N2 N 0.3251(2) 0.4042(2) 0.16604(10) 0.0554(4) Uani 1 1 d . . . . .
O3 O 0.6916(2) 0.3540(2) 0.27541(10) 0.0783(5) Uani 1 1 d . . . . .
C3 C 1.2045(6) 0.6914(10) 0.5121(2) 0.167(3) Uani 1 1 d . U . . .
H3 H 1.260785 0.707777 0.558168 0.200 Uiso 1 1 calc R U . . .
C4 C 1.2452(5) 0.7545(6) 0.4540(3) 0.1199(14) Uani 1 1 d . . . . .
H4 H 1.332394 0.814788 0.459283 0.144 Uiso 1 1 calc R U . . .
C5 C 1.1603(4) 0.7323(4) 0.38578(18) 0.0941(10) Uani 1 1 d . . . . .
H5 H 1.190392 0.779666 0.346067 0.113 Uiso 1 1 calc R U . . .
C6 C 1.0334(3) 0.6425(4) 0.37519(15) 0.0756(7) Uani 1 1 d . . . . .
C7 C 0.9419(3) 0.6131(3) 0.30048(14) 0.0712(6) Uani 1 1 d . . . . .
H7A H 0.954268 0.508793 0.288226 0.085 Uiso 1 1 calc R U . . .
H7B H 0.984259 0.673322 0.265353 0.085 Uiso 1 1 calc R U . . .
C8 C 0.7695(2) 0.6473(3) 0.29364(12) 0.0615(5) Uani 1 1 d . . . . .
H8 H 0.729593 0.603574 0.334931 0.074 Uiso 1 1 calc R U . . .
C9 C 0.7187(3) 0.8117(3) 0.28423(14) 0.0691(6) Uani 1 1 d . . . . .
C10 C 0.8403(4) 0.9300(4) 0.30687(18) 0.0892(9) Uani 1 1 d . . . . .
H10A H 0.924043 0.915871 0.280571 0.134 Uiso 1 1 calc R U . . .
H10B H 0.877725 0.921749 0.358035 0.134 Uiso 1 1 calc R U . . .
H10C H 0.796360 1.027489 0.296362 0.134 Uiso 1 1 calc R U . . .
C11 C 0.5757(4) 0.8404(5) 0.31711(19) 0.0968(10) Uani 1 1 d . . . . .
H11A H 0.535862 0.937912 0.302996 0.145 Uiso 1 1 calc R U . . .
H11B H 0.600986 0.835249 0.369086 0.145 Uiso 1 1 calc R U . . .
H11C H 0.499405 0.766098 0.300103 0.145 Uiso 1 1 calc R U . . .
C12 C 0.6508(2) 0.6929(3) 0.17292(13) 0.0611(5) Uani 1 1 d . . . . .
C13 C 0.6580(2) 0.4281(3) 0.22057(13) 0.0604(5) Uani 1 1 d . . . . .
C14 C 0.5936(2) 0.3575(3) 0.14854(12) 0.0589(5) Uani 1 1 d . . . . .
H14 H 0.582382 0.434076 0.110469 0.071 Uiso 1 1 calc R U . . .
C15 C 0.7106(3) 0.2386(4) 0.13275(17) 0.0856(8) Uani 1 1 d . . . . .
H15A H 0.805801 0.287832 0.126728 0.103 Uiso 1 1 calc R U . . .
H15B H 0.732978 0.171448 0.173971 0.103 Uiso 1 1 calc R U . . .
C16 C 0.6514(4) 0.1486(4) 0.06516(17) 0.0941(10) Uani 1 1 d . . . . .
H16A H 0.638042 0.213837 0.023070 0.113 Uiso 1 1 calc R U . . .
H16B H 0.726244 0.072403 0.058418 0.113 Uiso 1 1 calc R U . . .
C17 C 0.4997(4) 0.0751(3) 0.07143(17) 0.0880(9) Uani 1 1 d . . . . .
H17A H 0.514153 0.005189 0.111730 0.106 Uiso 1 1 calc R U . . .
H17B H 0.462200 0.019773 0.027339 0.106 Uiso 1 1 calc R U . . .
C18 C 0.3828(3) 0.1932(3) 0.08353(14) 0.0686(6) Uani 1 1 d . . . . .
H18A H 0.286296 0.144640 0.087951 0.082 Uiso 1 1 calc R U . . .
H18B H 0.364152 0.258816 0.041585 0.082 Uiso 1 1 calc R U . . .
C19 C 0.4362(2) 0.2869(2) 0.15160(12) 0.0559(5) Uani 1 1 d . . . . .
H19 H 0.449807 0.218302 0.193115 0.067 Uiso 1 1 calc R U . . .
C20 C 0.2039(3) 0.3434(3) 0.20280(13) 0.0680(6) Uani 1 1 d . . . . .
H20A H 0.165312 0.251703 0.178569 0.082 Uiso 1 1 calc R U . . .
H20B H 0.119416 0.414257 0.197864 0.082 Uiso 1 1 calc R U . . .
C21 C 0.2555(3) 0.3109(3) 0.28211(13) 0.0667(6) Uani 1 1 d . . . . .
C22 C 0.1989(6) 0.1897(5) 0.3135(2) 0.1116(13) Uani 1 1 d . . . . .
H22 H 0.130937 0.125044 0.285339 0.134 Uiso 1 1 calc R U . . .
C23 C 0.2420(8) 0.1625(7) 0.3871(3) 0.153(2) Uani 1 1 d . . . . .
H23 H 0.203350 0.078892 0.407612 0.184 Uiso 1 1 calc R U . . .
C24 C 0.3395(7) 0.2557(7) 0.4295(2) 0.1366(18) Uani 1 1 d . . . . .
H24 H 0.367524 0.236363 0.478921 0.164 Uiso 1 1 calc R U . . .
C25 C 0.3960(5) 0.3778(7) 0.3993(2) 0.1204(14) Uani 1 1 d . . . . .
H25 H 0.461666 0.443860 0.427954 0.145 Uiso 1 1 calc R U . . .
C26 C 0.3547(4) 0.4026(4) 0.32551(16) 0.0900(9) Uani 1 1 d . . . . .
H26 H 0.396024 0.484581 0.304823 0.108 Uiso 1 1 calc R U . . .
C27 C 0.2555(3) 0.4840(3) 0.09993(13) 0.0636(6) Uani 1 1 d . . . . .
H27A H 0.181052 0.418825 0.071141 0.076 Uiso 1 1 calc R U . . .
H27B H 0.335156 0.506495 0.071395 0.076 Uiso 1 1 calc R U . . .
C28 C 0.1764(2) 0.6280(3) 0.11509(12) 0.0598(5) Uani 1 1 d . . . . .
C29 C 0.2501(3) 0.7344(3) 0.16108(16) 0.0725(7) Uani 1 1 d . . . . .
H29 H 0.348723 0.714712 0.185760 0.087 Uiso 1 1 calc R U . . .
C30 C 0.1823(3) 0.8697(3) 0.17184(19) 0.0816(7) Uani 1 1 d . . . . .
H30 H 0.234992 0.939805 0.203431 0.098 Uiso 1 1 calc R U . . .
C31 C 0.0370(3) 0.9008(3) 0.13589(17) 0.0784(7) Uani 1 1 d . . . . .
H31 H -0.008221 0.992851 0.142103 0.094 Uiso 1 1 calc R U . . .
C32 C -0.0411(3) 0.7953(4) 0.09074(16) 0.0803(8) Uani 1 1 d . . . . .
H32 H -0.140683 0.814999 0.067261 0.096 Uiso 1 1 calc R U . . .
C33 C 0.0281(3) 0.6588(3) 0.07986(14) 0.0729(6) Uani 1 1 d . . . . .
H33 H -0.025298 0.587969 0.048908 0.087 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.192(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.401(7) . ?
C1 C6 1.346(5) . ?
N1 C8 1.470(3) . ?
N1 C12 1.395(3) . ?
N1 C13 1.403(3) . ?
O2 C9 1.466(3) . ?
O2 C12 1.340(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.336(9) . ?
N2 C19 1.489(3) . ?
N2 C20 1.466(3) . ?
N2 C27 1.468(3) . ?
O3 C13 1.214(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.324(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.363(4) . ?
C6 C7 1.513(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.534(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.538(4) . ?
C9 C10 1.515(4) . ?
C9 C11 1.512(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.508(3) . ?
C14 H14 0.9800 . ?
C14 C15 1.542(3) . ?
C14 C19 1.532(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.514(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.511(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.518(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.529(3) . ?
C19 H19 0.9800 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.503(3) . ?
C21 C22 1.365(4) . ?
C21 C26 1.363(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.383(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.354(8) . ?
C24 H24 0.9300 . ?
C24 C25 1.361(8) . ?
C25 H25 0.9300 . ?
C25 C26 1.384(5) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.513(3) . ?
C28 C29 1.370(3) . ?
C28 C33 1.389(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.378(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.371(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.371(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.394(4) . ?
C33 H33 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
C6 C1 C2 119.2(5) . . ?
C12 N1 C8 110.66(19) . . ?
C12 N1 C13 128.98(19) . . ?
C13 N1 C8 120.36(18) . . ?
C12 O2 C9 111.62(19) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 C1 122.5(5) . . ?
C3 C2 H2 118.8 . . ?
C20 N2 C19 112.08(19) . . ?
C20 N2 C27 109.81(17) . . ?
C27 N2 C19 112.61(17) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.0(4) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.1(5) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.6(4) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 117.6(3) . . ?
C1 C6 C7 120.1(3) . . ?
C5 C6 C7 122.3(3) . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C6 C7 C8 114.2(2) . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
N1 C8 C7 109.10(19) . . ?
N1 C8 H8 109.6 . . ?
N1 C8 C9 100.84(17) . . ?
C7 C8 H8 109.6 . . ?
C7 C8 C9 117.7(2) . . ?
C9 C8 H8 109.6 . . ?
O2 C9 C8 102.63(19) . . ?
O2 C9 C10 105.2(2) . . ?
O2 C9 C11 108.2(2) . . ?
C10 C9 C8 117.1(2) . . ?
C11 C9 C8 111.2(3) . . ?
C11 C9 C10 111.5(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 N1 129.2(2) . . ?
O1 C12 O2 122.7(2) . . ?
O2 C12 N1 108.11(19) . . ?
N1 C13 C14 120.6(2) . . ?
O3 C13 N1 117.5(2) . . ?
O3 C13 C14 121.8(2) . . ?
C13 C14 H14 109.4 . . ?
C13 C14 C15 107.11(18) . . ?
C13 C14 C19 110.32(18) . . ?
C15 C14 H14 109.4 . . ?
C19 C14 H14 109.4 . . ?
C19 C14 C15 111.2(2) . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 C14 112.1(2) . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 C15 110.6(3) . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C16 C17 H17A 109.7 . . ?
C16 C17 H17B 109.7 . . ?
C16 C17 C18 109.9(2) . . ?
H17A C17 H17B 108.2 . . ?
C18 C17 H17A 109.7 . . ?
C18 C17 H17B 109.7 . . ?
C17 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C17 C18 C19 112.4(2) . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
N2 C19 C14 110.08(17) . . ?
N2 C19 C18 114.52(17) . . ?
N2 C19 H19 107.1 . . ?
C14 C19 H19 107.1 . . ?
C18 C19 C14 110.46(19) . . ?
C18 C19 H19 107.1 . . ?
N2 C20 H20A 108.7 . . ?
N2 C20 H20B 108.7 . . ?
N2 C20 C21 114.13(18) . . ?
H20A C20 H20B 107.6 . . ?
C21 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
C22 C21 C20 120.3(3) . . ?
C26 C21 C20 121.9(2) . . ?
C26 C21 C22 117.8(3) . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.4(4) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 121.0(4) . . ?
C24 C23 H23 119.5 . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.4(4) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 120.4 . . ?
C24 C25 C26 119.2(4) . . ?
C26 C25 H25 120.4 . . ?
C21 C26 C25 122.2(3) . . ?
C21 C26 H26 118.9 . . ?
C25 C26 H26 118.9 . . ?
N2 C27 H27A 108.9 . . ?
N2 C27 H27B 108.9 . . ?
N2 C27 C28 113.37(19) . . ?
H27A C27 H27B 107.7 . . ?
C28 C27 H27A 108.9 . . ?
C28 C27 H27B 108.9 . . ?
C29 C28 C27 121.50(19) . . ?
C29 C28 C33 118.0(2) . . ?
C33 C28 C27 120.4(2) . . ?
C28 C29 H29 119.1 . . ?
C28 C29 C30 121.9(2) . . ?
C30 C29 H29 119.1 . . ?
C29 C30 H30 120.1 . . ?
C31 C30 C29 119.9(3) . . ?
C31 C30 H30 120.1 . . ?
C30 C31 H31 120.2 . . ?
C30 C31 C32 119.6(3) . . ?
C32 C31 H31 120.2 . . ?
C31 C32 H32 119.9 . . ?
C31 C32 C33 120.3(2) . . ?
C33 C32 H32 119.8 . . ?
C28 C33 C32 120.2(3) . . ?
C28 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 1.1(13) . . . . ?
C1 C6 C7 C8 56.7(5) . . . . ?
N1 C8 C9 O2 -23.6(2) . . . . ?
N1 C8 C9 C10 -138.2(2) . . . . ?
N1 C8 C9 C11 91.9(2) . . . . ?
N1 C13 C14 C15 120.3(3) . . . . ?
N1 C13 C14 C19 -118.6(2) . . . . ?
C2 C1 C6 C5 2.8(9) . . . . ?
C2 C1 C6 C7 -179.8(6) . . . . ?
C2 C3 C4 C5 1.0(10) . . . . ?
N2 C20 C21 C22 -143.8(3) . . . . ?
N2 C20 C21 C26 38.6(4) . . . . ?
N2 C27 C28 C29 51.7(3) . . . . ?
N2 C27 C28 C33 -131.2(2) . . . . ?
O3 C13 C14 C15 -56.7(3) . . . . ?
O3 C13 C14 C19 64.5(3) . . . . ?
C3 C4 C5 C6 -1.3(8) . . . . ?
C4 C5 C6 C1 -0.7(7) . . . . ?
C4 C5 C6 C7 -178.1(4) . . . . ?
C5 C6 C7 C8 -125.9(3) . . . . ?
C6 C1 C2 C3 -3.1(13) . . . . ?
C6 C7 C8 N1 -166.8(2) . . . . ?
C6 C7 C8 C9 79.2(3) . . . . ?
C7 C8 C9 O2 94.9(2) . . . . ?
C7 C8 C9 C10 -19.7(3) . . . . ?
C7 C8 C9 C11 -149.6(2) . . . . ?
C8 N1 C12 O1 169.2(2) . . . . ?
C8 N1 C12 O2 -10.6(2) . . . . ?
C8 N1 C13 O3 5.2(3) . . . . ?
C8 N1 C13 C14 -171.91(19) . . . . ?
C9 O2 C12 O1 173.7(2) . . . . ?
C9 O2 C12 N1 -6.6(3) . . . . ?
C12 N1 C8 C7 -102.9(2) . . . . ?
C12 N1 C8 C9 21.7(2) . . . . ?
C12 N1 C13 O3 -174.8(2) . . . . ?
C12 N1 C13 C14 8.1(4) . . . . ?
C12 O2 C9 C8 19.7(3) . . . . ?
C12 O2 C9 C10 142.8(2) . . . . ?
C12 O2 C9 C11 -97.9(3) . . . . ?
C13 N1 C8 C7 77.1(3) . . . . ?
C13 N1 C8 C9 -158.3(2) . . . . ?
C13 N1 C12 O1 -10.8(4) . . . . ?
C13 N1 C12 O2 169.4(2) . . . . ?
C13 C14 C15 C16 174.3(3) . . . . ?
C13 C14 C19 N2 62.0(2) . . . . ?
C13 C14 C19 C18 -170.59(19) . . . . ?
C14 C15 C16 C17 -56.6(4) . . . . ?
C15 C14 C19 N2 -179.34(19) . . . . ?
C15 C14 C19 C18 -51.9(2) . . . . ?
C15 C16 C17 C18 58.0(3) . . . . ?
C16 C17 C18 C19 -58.2(3) . . . . ?
C17 C18 C19 N2 -179.8(2) . . . . ?
C17 C18 C19 C14 55.2(3) . . . . ?
C19 N2 C20 C21 75.5(3) . . . . ?
C19 N2 C27 C28 -164.74(19) . . . . ?
C19 C14 C15 C16 53.7(3) . . . . ?
C20 N2 C19 C14 -152.84(18) . . . . ?
C20 N2 C19 C18 82.0(2) . . . . ?
C20 N2 C27 C28 69.6(3) . . . . ?
C20 C21 C22 C23 -177.7(4) . . . . ?
C20 C21 C26 C25 176.4(4) . . . . ?
C21 C22 C23 C24 0.7(9) . . . . ?
C22 C21 C26 C25 -1.3(5) . . . . ?
C22 C23 C24 C25 -0.1(9) . . . . ?
C23 C24 C25 C26 -1.2(8) . . . . ?
C24 C25 C26 C21 1.9(7) . . . . ?
C26 C21 C22 C23 0.0(6) . . . . ?
C27 N2 C19 C14 82.8(2) . . . . ?
C27 N2 C19 C18 -42.4(3) . . . . ?
C27 N2 C20 C21 -158.5(2) . . . . ?
C27 C28 C29 C30 176.0(3) . . . . ?
C27 C28 C33 C32 -176.3(2) . . . . ?
C28 C29 C30 C31 -0.1(5) . . . . ?
C29 C28 C33 C32 1.0(4) . . . . ?
C29 C30 C31 C32 1.5(5) . . . . ?
C30 C31 C32 C33 -1.7(5) . . . . ?
C31 C32 C33 C28 0.4(4) . . . . ?
C33 C28 C29 C30 -1.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.279
_oxdiff_exptl_absorpt_empirical_full_min 0.610
